John Cruickshank began a long association with the OCAA that began in 1969 when he became Athletic Director of Sheridan College. Cruickshank built the Sheridan athletic program from its beginnings before moving over to Seneca College in 1979.

Cruickshank was the OCAA's President from 1975 to 1977 and then moved onto the CCAA in 1979 where he was an Executive Committee member until 1985. As an OCAA Convenor, Cruickshank oversaw cross-country running in 1969-70, judo in 1970-71 and 1972-73, and curling from 1978 to 1980.

In 1985, the OCAA presented Cruickshank with a Shield Award to recognize his contributions to the association.